LocationMiami, Mississauga, Remote, Florida, United States, Ontario, Canada
Work moderemote
Typefull-time
DepartmentProfessional Services
Company size11+ people
First seen1mo ago
Last seen1d ago
About Upshop
Upshop is the market leader in Total Store Operations solutions for the Grocery and C-Store markets. We offer an AI-powered, SaaS platform connecting Fresh, Center, eCommerce, and DSD department operations to deliver a simplified, smarter, more connected store experience. Customers running Upshop realize significant improvements in sales, shrink, food safety and sustainability across the entire store. 150+ retail chain accounts trust our software in over 30k+ stores, 9 countries, and 3 continents.
Role Overview
Upshop is seeking a Director of Implementation to lead our Implementation organization and drive successful customer deployments across our Total Store Operations platform.
This leader is responsible for developing and mentoring a high-performing team of Implementation Managers and Consultants while ensuring customers achieve successful business outcomes throughout their implementation journey.
The ideal candidate combines enterprise SaaS implementation leadership with a strong understanding of retail operations, preferably within grocery, convenience, or food retail environments. This individual will serve as a trusted advisor to customers, a mentor to implementation leaders, and a key contributor in scaling Upshop’s Professional Services organization.
The Director of Implementation will also lead the evolution of Upshop’s implementation practices, championing automation, AI-enabled delivery capabilities, and operational excellence initiatives that improve efficiency, accelerate customer outcomes, and create a more scalable and consistent delivery model.
Key Responsibilities
Team Leadership & Talent Development
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Lead, mentor, and develop a team of Implementation Managers, Senior Consultants, and Implementation Consultants.
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Foster a culture of accountability, continuous learning, collaboration, and customer obsession.
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Establish clear performance expectations, coaching programs, career development plans, and succession strategies.
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Drive implementation methodology adoption, process consistency, and operational excellence across the team.
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Partner with Professional Services leadership on organizational planning, hiring, onboarding, and workforce development.
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Develop implementation Centers of Excellence and reusable delivery assets that scale knowledge across the organization.
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Lead the ongoing evolution of Upshop’s implementation methodology, delivery frameworks, and best practices.
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Identify opportunities to leverage automation, AI, and digital tooling to improve implementation efficiency, consistency, and customer outcomes.
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Foster a culture of innovation and adoption of emerging technologies that enhance customer delivery.
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Establish measurable delivery standards and KPIs focused on customer adoption, implementation quality, operational efficiency, and team development.
Customer Engagement & Delivery Leadership
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Serve as an executive sponsor and escalation point for strategic customer implementations.
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Build trusted relationships with customer sponsors, operational leaders, IT stakeholders, and executive teams.
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Ensure customer objectives, adoption goals, and success metrics are clearly defined and achieved.
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Guide implementation teams through complex deployments, organizational change initiatives, testing, launch activities, and post-launch adoption.
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Lead risk identification, mitigation planning, and issue resolution efforts across the implementation portfolio.
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Partner closely with Customer Success to ensure smooth transitions from implementation to long-term customer adoption and value realization.
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Collaborate with Sales and Solution Consulting to ensure customer expectations, implementation strategies, and success criteria are aligned from project inception.
Implementation Excellence
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Own implementation delivery standards, methodologies, playbooks, and best practices across the organization.
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Drive consistency across project planning, discovery, solution design, configuration, testing, training, launch, and hypercare activities.
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Capture lessons learned and continuously improve implementation frameworks and operational processes.
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Ensure implementations are delivered on time, within scope, within budget, and aligned to customer business outcomes.
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Establish governance models that improve visibility, accountability, risk management, and delivery quality.
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Partner with PMO leadership to improve delivery governance, forecasting, resource planning, and project execution.
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Drive continuous improvement initiatives that reduce implementation timelines while maintaining exceptional customer outcomes.
Technical Leadership
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Maintain deep knowledge of Upshop’s platform architecture, data structures, integrations, and implementation requirements.
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Provide guidance on solution architecture, data migration, system configuration, integration strategy, and technical deployment approaches.
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Support complex integrations involving ERP, forecasting, inventory, ordering, POS, DSD, EDI, eCommerce, and other retail technology ecosystems.
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Partner with Product and Engineering to improve implementation tooling, onboarding workflows, automation capabilities, and customer enablement resources.
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Develop organizational expertise around modern cloud technologies, data platforms, integration frameworks, and scalable implementation approaches.
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Maintain working knowledge of Microsoft Azure technologies, including Azure SQL Database, Azure Cosmos DB, APIs, data integration patterns, and cloud-based application architectures.
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Champion the use of AI-enabled tools to improve project delivery, testing, documentation, training, knowledge management, customer onboarding, and internal operational efficiency.
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Leverage data and analytics to identify trends, improve delivery performance, and enhance customer outcomes.
Operational Leadership
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Monitor implementation portfolio health through operational, financial, and customer success metrics.
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Oversee implementation forecasting, staffing, utilization, and capacity planning.
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Support Statement of Work reviews, implementation estimates, change requests, and delivery commitments.
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Ensure resource allocation aligns with strategic priorities and customer commitments.
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Provide executive reporting on implementation performance, customer health, delivery risks, and organizational trends.
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Partner across Product, Support, Customer Success, Sales, and Professional Services to continuously improve the end-to-end customer experience.
Required Qualifications
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Bachelor’s degree in Business, Information Systems, Computer Science, Supply Chain, Retail Operations, and/or related field/experience.
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5+ years of experience leading enterprise software, SaaS, or technology implementations.
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3+ years of people leadership experience managing implementation, consulting, delivery, or professional services teams.
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Proven experience leading customer-facing delivery organizations supporting enterprise customers.
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Demonstrated success building, mentoring, and developing high-performing teams.
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Strong knowledge of SaaS implementation methodologies and software deployment practices.
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Experience managing multiple concurrent implementations and complex customer engagements.
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Exceptional communication, stakeholder management, executive presentation, and relationship-building skills.
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Strong analytical, problem-solving, and decision-making capabilities.
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Ability to travel up to 25%.
Preferred Qualifications
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Grocery retail, food retail, convenience retail, or store operations experience strongly preferred.
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Experience with forecasting, ordering, inventory, supply chain, fresh operations, DSD, merchandising, workforce management, or store execution solutions strongly preferred.
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Experience with Microsoft Azure technologies, including Azure SQL Database, Azure Cosmos DB, cloud data platforms, and enterprise integration architectures.
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Strong understanding of data architecture, system integrations, APIs, EDI, and enterprise application ecosystems.
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Experience leveraging AI-enabled tools, automation platforms, or emerging technologies to improve operational efficiency and customer outcomes.
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Working knowledge of SQL, databases, Excel, and analytical tools.
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Experience with Salesforce, Zendesk, Jira, Wrike, or similar enterprise platforms.
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Experience scaling implementation organizations within high-growth SaaS environments.
Success Profile
The successful candidate:
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Is a people-first leader who develops teams, mentors future leaders, and creates a culture of accountability and continuous improvement.
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Builds trust with customer executives and serves as a strategic advisor throughout the implementation journey.
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Understands grocery and retail operations and can translate customer objectives into scalable implementation strategies.
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Balances strategic leadership with hands-on execution when customer success requires it.
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Uses metrics and data-driven decision making to improve delivery performance and customer outcomes.
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Embraces innovation and continuously seeks opportunities to modernize implementation practices through automation, AI, and scalable delivery frameworks.
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Drives cross-functional alignment while maintaining a relentless focus on customer value realization.